2-Chloro-6-methylphenyl isocyanate → N-(2-hydroxy-4-nitrophenyl) N'-(2-chloro 6-methylphenyl)urea

HRID 612651Notes

Reaction equation

HRID 612651 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[N:20]=[C:21]=[O:22]>>[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]([NH:20][C:14]1[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=1[Cl:12])=[O:22]

Participants

3

Reactant 2

HCID 2681232-Chloro-6-methylphenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 19595671N-(2-hydroxy-4-nitrophenyl) N'-(2-chloro 6-methylphenyl)ureaYield 29%

Procedure

The urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-chloro 6-methyl phenyl isocyanate by general Method B. It was purified by dilution with methylene chloride and precipitation with hexane. Filtering afforded the desired compound (0.31 g, 29%). EI-MS m/z 322 (M+H)+

Workup

  1. customIt was purified by dilution with methylene chloride and precipitation with hexane
  2. filtrationFiltering

Sources & evidence

ORD record
ord-54b46baf0dd84441bf065e003afd234b
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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